The present invention relates to a genus of compounds having the generic structure: ##STR3## wherein X is a moiety selected from the group consisting of ##STR4## and wherein R.sub.1 and R.sub.2 are different, one of R.sub.1 or R.sub.2 being methyl, and the other of R.sub.1 or R.sub.2 being ethyl, or mixtures of same, and novel compositions using members of such genus of compounds or mixtures of same to augment, modify or enhance the flavor and/or aroma of consumable materials or impart flavor and/or aroma to consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors and aromas to (or in) various consumable materials such as foodstuffs having chocolate, cocoa butter, milk, vanilla, blackberry, cooked vegetable, stew, cooked green vegetable and baked goods flavors and tobaccos which have been produced from reconstituted tobacco having imparted thereto distinctive, pleasing chocolate flavor nuances, or tobaccos having nutty, green and burnt roasted flavor and aroma chatacteristics prior to and on smoking. These substances are used to diminish the use of natural materials, some of which may be in short supply, and to provide more uniform properties in the finished product.
Sweet, dairy-like, creamy, vanilla, berry, milk chocolate-like, chocolate, green pepper, cooked green pepper, spicey, peppery, meaty, roasted, and cocoa butter-like aromas as well as sweet, dairy-like, creamy, vanilla, berry, milk chocolate, green pepper, cooked green pepper, nutty, spicey, peppery, meaty, roasted, chocolate and cocoa butter-like flavor characteristics are particularly desirable for many uses in foodstuff flavors, chewing gum flavors, toothpaste flavors, and medicinal product flavors.
Chocolate-like aromas with cocoa-like and sweet, creamy nuances or nutty, green, burnt roasted aromas prior to smoking, and chocolate-like aroma notes and more tobacco-like smoke aroma characteristics in the main stream and side stream on smoking are desirable in tobaccos and in tobacco flavoring compositions.
German Auslegschrift No. 2,402,416 discloses a sublimable performed composition in tablet form containing 1,3,5-triisopropyl-s-trioxane or 1,3,5-tri-t-butyl-s-trioxane as an active agent whereby the composition may be used to deodorize toilets, telephone mouthpieces, or give off insecticides.
2,4,6-Tri-s-butyl-1,3,5-trioxane is disclosed at Volume 19, page 391 of Beilstein; and it is further disclosed to be a "trimer" of methyl ethyl acetaldehyde (2-methyl butanal). An additional disclosure in Beilstein is at Volume 19, supplement 2 at page 403. Neither Beilstein reference discloses the organoleptic qualities of 2,4,6-triisobutyl-1,3,5-trioxane.
Indeed, the 1,3,5-triisopropyl-s-trioxane has little, if any, aroma or flavor to be of value in flavoring foodstuffs or tobaccos. It is, accordingly, quite surprising that the next adjacent methyl homologue, 2,4,6-triisobutyl-1,3,5-trioxane, has such intense aroma and flavor nuances as described herein.
Trialkyl substituted oxazolines are described in the prior art as being useful for modifying fish flavors in U.S. Pat. No. 3,627,540 issued on Dec. 14, 1971. More specifically, it is stated at Column 2, lines 12-27:
The seafood flavor characteristic of the pentadienal can further be varied by including one or more cyclic oxazo compounds, particularly .DELTA..sup.3 -oxazolines having the formula ##STR5## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen, alkyl, or alkylene and can be the same or different. It is preferred in certain embodiments of the present invention to use lower alkyl derivatives of oxazoline, preferably those having up to about three carbon atoms in the alkyl group or groups. A preferred oxazoline in certain embodiments of the invention is 2,4,5-trimethyl-.DELTA..sup.3 -oxazoline. U.S. Pat. No. 3,627,540 does not imply, however, that the higher alkyl oxazoline analogue of the instant invention taken alone or in admixture with the 2,4,6-triisobutyl-1,3,5-trioxane of our invention, have flavor and aroma nuances of such quality and intensity as described herein.
Mussinan et al, "Identification and Flavor Properties of Some 3-Oxazolines and 3-Thiazolines Isolated from Cooked Beef," Abstracts of Papers, 170th Meeting, American Chemical Society, August 24-29, 1975, Port City Press, Baltimore, Maryland, Item No. AGFD 022, states:
.sup.22. IDENTIFICATION AND FLAVOR PROPERTIES OF SOME 3-OXAZOLINES AND 3-THIAZOLINES ISOLATED FROM COOKED BEEF. Cynthia J. Mussinan, Richard A. Wilson, Ira Katz, Anne Sanderson, and Manfred H, Vock. International Flavors and Fragrances, Inc., 1515 Highway 36, Union Beach, New Jersey 07735.
Four 3-oxazolines and two 3-thiazolines have been isolated from beef cooked in a sealed stainless steel vessel at 162.7.degree. and 182.degree.. The compounds were identified by matching retention times and mass spectra with those of authentic compounds synthesized in our laboratory. The compounds identified were 2,4-dimethyl-3-oxazoline; 2,4,5-trimethyl-3-oxazoline; 2,4-dimethyl-5-ethyl-3-oxazoline; 2,5-dimethyl-4-ethyl-3-oxazoline; 2,4-dimethyl-3-thiazoline; and 2,4,5-trimethyl-3-thiazoline. The synthesis, spectra and flavor properties of these and some related compounds will be discussed. None of the oxazoline compounds of Mussinan et al. have properties even remotely similar to those of the compounds containing the oxazoline moieties of the instant invention. Thus, the compounds containing the oxazoline moieties of the instant invention have unexpected, unobvious and advantageous properties with respect to their organoleptic characteristics when compared with the oxazolines of Mussinan et al. and U.S. Pat. No. 3,627,540.